5-(1H-benzimidazol-3-ium-2-yl)-2-hydroxybenzoate | 1297611-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-(1H-benzimidazol-3-ium-2-yl)-2-hydroxybenzoate
• 英文别名: 5-(benzimidazolium-2-yl)salicylate；5-(1H-benzimidazol-2-yl)-2-hydroxybenzoic acid
• CAS: 1297611-18-7
• 化学式: C₁₄H₁₀N₂O₃
• 分子量: 254.245
• InChiKey: IXCMYXKERPMGPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲酰水杨酸 、 邻苯二胺 以 乙醇 为溶剂， 反应 6.0h， 以84%的产率得到5-(1H-benzimidazol-3-ium-2-yl)-2-hydroxybenzoate
  参考文献：
  名称：

  5-Formylsalicylic acid and 5-(benzimidazolium-2-yl)salicylate

  摘要：

  Both title compounds are derivatives of salicylic acid. 5-Formylsalicylic acid (systematic name: 5-formyl-2-hydroxybenzoic acid), C8H6O4, possesses three good hydrogen-bond donors and/or acceptors coplanar with their attached benzene ring and abides very well by Etter's hydrogen-bond rules. Intermolecular O-H center dot center dot center dot O and some weak C-H center dot center dot center dot O hydrogen bonds link the molecules into a planar sheet. Reaction of this acid and o-phenylenediamine in refluxing ethanol produced in high yield the new zwitterionic compound 5-(benzimidazolium-2-yl) salicylate [systematic name: 5-(1H-benzimidazol-3-ium-2-yl)-2-hydroxybenzoate], C14H10N2O3. Each imidazolium N-H group and its adjacent salicyl C-H group chelate one carboxylate O atom via hydrogen bonds, forming seven-membered rings. As a result of steric hindrance, the planes of the molecules within these pairs of hydrogen-bonded molecules are inclined to one another by similar to 74 degrees. There are also pi-pi stacking interactions between the parallel planes of the imidazole ring and the benzene ring of the salicyl component of the adjacent molecule on one side and the benzimidazolium component of the molecule on the other side.

  DOI：

  10.1107/s0108270110044926